Skiing at Smiling Hill Farm

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What if I told you there was a magical place in southern Maine where you could enjoy 25k of skiing/snowshoeing trails, homemade ice cream, and cute farm animals in the middle of winter?! Does it sound too good to be true?! Well, it isn’t. You can experience all of these things (and so much more!) at Smiling Hill Farm. Oh, and I forgot to mention the best part. You can bring your dog!

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Smiling Hill Farm is a 500-acre working farm that has been operating since the 1600s. It is now being run by the 12th generation of the Knight family. It is home to purebred Holstein dairy cows as well as some other pretty cute farm animals. Conveniently located within 20 minutes from Portland, Smiling Hill Farm is accessible, yet remote. It’s located right off route 22 in Westbrook, known to some as County Road. After turning off the main road and haulin’ ass up their long driveway, there will be a large, paved parking lot on top of the hill to the right. This is where I parked to go cross-country skiing.

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After parking, I made my way to the ski center and purchased a ticket. The staff were friendly and helpful. They offered me rental equipment and recommended a couple of trails. Because I was skiing mid-week and had my own equipment, my ticket was only $10. The amount I paid to ski was relatively inexpensive compared to other cross-country skiing places i’ve been to in southern Maine. I grabbed a trail map and headed towards the trails.

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Using the very sophisticated eeny meeny miny moe decision-making process, I made my way to Wood Duck Trail. On the way, I was very pleasantly surprised to find some of the world’s cutest cows. I swear they strategically placed these cows to lure me into buying a season pass. But hey, it worked. I have no regrets.

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After saying goodbye to the cows, I strapped on my skis and began skiing through the open fields and wooded terrain on the Wood Duck Trail. Shortly after, I turned right onto the Deer Run Trail. This was a nice, quiet wooded trail that brought me over two quaint bridges.

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There were a number of trails that stood out to me on this adventure. There was the plantation pine trail, which featured a wide trail surrounded by pine trees. Holstein Hill, which provided a decent uphill climb and views of the surrounding area. Bull Run, which brought me down a nice, gradual downhill.

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Last, but not least, was Pine Tree Path. A gorgeous, narrow trail that brought me into a Narnia-esque tunnel of gorgeous, 45-year-old pine trees. They looked especially lovely blanketed in fresh snow. After exploring the east side trails, it was time for lunch.

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After eating lunch, I decided to explore the west side trails, starting with the Sugar Maple Trail. It began with a small downhill, which led me to a VERY pleasant surprise. Pigs! The darn cutest pigs I had ever seen! They all came running over, chatting up a storm. I was in heaven.

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After visiting the pigs, I continued on to The Barnyard Trail, which brought me right to the deer pen. They were graceful and a bit shy, but oh so beautiful. I absolutely did not expect to see so many animals on my outing. They really were the icing on the cake.

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At the end of the Barnyard Trail, I found the Sugar Maple Trail, which brought me to a neat, run-down log cabin. It had a sign that I thought said Nate’s place (which made me chuckle—because my husband, Nate, always jokes about living in a cabin off-the-grid) but after looking reallllly close at pictures of the sign, I think it said Mate’s Place. Hmm... Odd?

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After crossing over to the White Pine Trail, followed by the Wild Turkey Trail, I jumped back on the winding Sugar Maple Trail to get back to the ski center. Before leaving, I paid a visit to the Smiling Hill Farm dairy store to get myself a quart of flavored milk. It was SO hard to choose a flavor. They had coffee, blueberry, strawberry, chocolate, vanilla creme, orange creme, banana, etc. I ended up going with my tried and true: chocolate milk. They also had an impressive assortment of dairy products and lunch items for sale.

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The trails at Smiling Hill Farm were fun, well-maintained, and beautiful. They were a welcomed escape from city living, without having to drive hours. I enjoyed my experience so much that I went back two days later with my husband and bought a season pass. I highly encourage you to grab some loved ones and head over to experience a great Maine adventure! Don’t even think about leaving without some chocolate milk AND homemade ice cream!

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3 Must-Do Hikes in Southern Maine